L-P-HYDROXYPHENYLGLYCINE METHYL EST
- Product Name
- L-P-HYDROXYPHENYLGLYCINE METHYL EST
- CAS No.
- 127369-30-6
- Chemical Name
- L-P-HYDROXYPHENYLGLYCINE METHYL EST
- Synonyms
- Amoxicillin Impurity 19;Cefadroxil Impurity 9 HCl;Cefadroxil Impurity 11 HCl;L-P-HYDROXYPHENYLGLYCINE METHYL EST;Methyl L-(-)-4-Hydroxyphenylglycinate;methyl (2S)-2-amino-2-(4-hydroxyphenyl)acetate;Methyl L-(-)-4-Hydroxyphenylglycinate(HCl Salt);(S)-Methyl 2-amino-2-(4-hydroxyphenyl)acetate HCl;S-4-Hydroxyphenylglycine methyl ester hydrochloride;(S)-Methyl 2-amino-2-(4-hydroxyphenyl)acetate HCl ee
- CBNumber
- CB0504629
- Molecular Formula
- C9H12ClNO3
- Formula Weight
- 217.64948
- MOL File
- 127369-30-6.mol
L-P-HYDROXYPHENYLGLYCINE METHYL EST Property
- Melting point:
- 179-183 °C(lit.)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- color
- White
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- M339063
- Product name
- Methyl(2S)-2-amino-2-(4-hydroxyphenyl)acetateHydrochloride
- Packaging
- 1g
- Price
- $130
- Updated
- 2021/12/16
- Product number
- AS46513-B
- Product name
- (S)-Methyl 2-amino-2-(4-hydroxyphenyl)acetate HCl
- Purity
- 95% ee
- Packaging
- 1g
- Price
- $79
- Updated
- 2021/12/16
- Product number
- AS46513-B
- Product name
- (S)-Methyl 2-amino-2-(4-hydroxyphenyl)acetate HCl
- Purity
- 95% ee
- Packaging
- 5G
- Price
- $217
- Updated
- 2021/12/16
- Product number
- 4799CU
- Product name
- (S)-Methyl2-amino-2-(4-hydroxyphenyl)acetatehydrochloride
- Packaging
- 25g
- Price
- $487
- Updated
- 2021/12/16
- Product number
- AS46513-B
- Product name
- (S)-Methyl 2-amino-2-(4-hydroxyphenyl)acetate HCl
- Purity
- 95% ee
- Packaging
- 25g
- Price
- $596
- Updated
- 2021/12/16
L-P-HYDROXYPHENYLGLYCINE METHYL EST Chemical Properties,Usage,Production
Uses
Methyl (2S)-2-amino-2-(4-hydroxyphenyl)acetate Hydrochloride acts as a reagent in the synthesis of Amoxicillin, an antibiotic for the treatment of bacterial infection.
Synthesis
67-56-1
22818-40-2
57591-61-4
General procedure for the synthesis of D-p-hydroxyphenylglycine methyl ester hydrochloride from methanol and (R)-2-amino-2-(4-hydroxyphenyl)acetic acid: under nitrogen protection and -15 °C, thionyl chloride (1.5 mL, 33.0 mmol) was slowly added dropwise to anhydrous methanol (25 mL) in (R)-4-hydroxyphenylglycine (5.00 g, 29.91 mmol) ) suspension while stirring. The reaction mixture was gradually warmed to room temperature and stirred continuously overnight. Subsequently, the yellow solution was refluxed for 30 min. The reaction mixture was concentrated under reduced pressure to give D-p-hydroxyphenylglycine methyl ester hydrochloride in the form of an off-white solid. The hydrochloride was stirred in ether (15 mL), filtered, washed with ether (2 x 15 mL) and dried to give the final D-p-hydroxyphenylglycine methyl ester hydrochloride (6.50 g, 100%) as a white solid with a melting point of 189-191 °C; specific optical rotation [α]20D = -120.9 (c 1, 1M HCl), literature value [α]25D = - 121.1 (c 1, 1M HCl); IR spectra (KBr) νmax/cm-1: 3339 (broad peak), 1740 (C=O), 1595; NMR hydrogen spectrum (300 MHz, DMSO-d6) δH: 3.68 (3H, single peak, OCH3), 5.11 (1H, single peak, C(2)H), 6.80 (2H, double peak. J=8.5 Hz, aromatic H), 7.25 (2H, double peak, J=8.5 Hz, aromatic H), 8.70 (3H, broad peak, NH3), 9.86 (1H, single peak, OH).
References
[1] Tetrahedron Asymmetry, 2013, vol. 24, # 20, p. 1265 - 1275
[2] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 649 - 660
[3] Synthesis, 2012, vol. 44, # 6, p. 875 - 880
[4] Croatica Chemica Acta, 2003, vol. 76, # 1, p. 23 - 36
[5] Heterocycles, 2009, vol. 78, # 6, p. 1477 - 1483
L-P-HYDROXYPHENYLGLYCINE METHYL EST Preparation Products And Raw materials
Raw materials
Preparation Products
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